Apple Inc. founder Steve Jobs and British entrepreneur Richard Branson couldn’t be more opposite in their leadership styles but they apparently admired each other.

In Apple’s famous 1997 “Think Different” commercial, which crystallized the brand at the time, Mr. Jobs narrated: “Here’s to the crazy ones. The misfits. The rebels. The troublemakers. The round pegs in the square holes. The ones who see things differently.”

Gareth Brennan, president and founder of Eventscape Photo by Rosa Park shot in Etobicoke August 2014

Winner

Sir Richard was touched: “I am proud to say that, in the accompanying montage, he counted me as one of them. I think it’s an attitude that’s shared by all leaders who make a difference – and it’s one reason why, despite our vastly different styles, Steve Jobs was always the entrepreneur whom I most admired,” he wrote in The Telegraph in London after Mr. Jobs died in 2011.

While Mr. Jobs was autocratic, meticulous, detail-oriented and obsessed with control, Sir Richard says his style is the reverse – but they were alike in many other ways.

“Steve Jobs wasn’t known for his sense of fun, but he was always at the centre of everything Apple did,” Sir Richard wrote in tribute. “Over his extraordinary career, he learned the same lesson I have – that even when you’re successful, it is vital that you don’t solely lead your company from a distance. Walk the floor, get to know your people.”

At the time the commercial was airing, Sir Richard was already a serial entrepreneur whose track record stretched back to starting a magazine, Student, in the crypt of a church while a teenager in the 1970s.

At 16, Sir Richard dropped out of school and, seeing the explosion in popular music driven by the baby boomers, he and his friends shifted into selling record albums by mail order, undercutting the Main Street retailers who priced in lockstep with huge mark-ups.

They called their fledgling venture, Virgin, on the premise it was all new to them. It grew to become a recording label with acts such as Mike Oldfield and The Sex Pistols – and it created a rich cash flow that allowed him to buy his own island in his late 20s and spread into other areas of business.

In 1984, Sir Richard surprised everyone by launching an airline simply because he was unhappy with the status quo.

“I flew all over the world on other people’s airlines because of our record labels,” he said. “I hated the experience. I mean, you got a lump of chicken, if you were lucky, dumped into your lap. There was no entertainment. The crews didn’t seem to be very happy.”

He decided to create his own airline. With a call to Boeing, he had a plane.

“They said, ‘What’s the name of your company?’” he told Mr. Beck. “I said, ‘Virgin.’ I take my hat off to them, because they just said, ‘Well, look, as long as you go further than your name suggests, we’ll give you a 747.’”

Many other ventures have followed: Virgin Mobile, Virgin Trains, Virgin Cola, Virgin Vodka and more recently, perhaps the most outrageous, or most visionary, depending on your point of view, Virgin Galactic, which promises to make space tourism a reality. In all there have been some 400 Virgin derivatives.

As a chief spokesman and highly visible brand promoter, Sir Richard – he was bestowed his knighthood in 1999 – has few equals. He is brash, outspoken and loves to make grand entrances, such as arriving at media events by zip line or parachute.

He is an extreme sports enthusiast who loves ballooning, ocean-racing yachts and kite surfing with a devil-may-care attitude, shoulder length, sun-bleached blonde hair and a megawatt smile made for the front page.

Behind the scenes, however, Sir Richard is much more calculated. While he is willing to assume risk, he never takes chances on being unprepared, he says. And being different is always out front.

“Don’t think, what’s the cheapest way to do it or what’s the fastest way to do it,” he writes on his blog at Virgin.com. “Think, what’s the most amazing way to do it?”

While he has a reputation as a “yes” man to his own people, copiously taking notes in his black and red ledger book, always willing to green light an initiative or concept to see how it plays out, he also has a steely resolve not to be taken lightly.

When British Airways launched a series of dirty tricks against his upstart Virgin Airlines, Sir Richard dug in and fought back against the giant carrier with a lawsuit, winning a $5.8-million (including legal costs) settlement, which he promptly distributed among his staff as the “BA bonus.”

Two years ago when Virgin Trains failed to win the bidding to continue operating the busy West Coast Main Line in England, Sir Richard sued again, claiming the bid process was botched. An internal government review proved him right and Virgin was put back in charge through 2016, when it expects to bid again.

Sir Richard’s success is also based on the extreme customer focus of all Virgin’s ventures. Whether launching a limobike airport express service for Virgin Airlines passengers – a motorcycle and sidecar limousine to beat London traffic – or a cocktail bar at 40,000 feet, it’s always about the customer experience.

“You have to ask the question, ‘What is a business?’ ” he told a New Zealand interviewer in 2011. “It’s creating something which makes a difference in other people’s lives, whether that’s an airline, a music company or sending people into space that they couldn’t otherwise afford to do.”

On his blog he quotes a TED talk from author and business philosopher Simon Sinek, who evangelizes that success is determined by knowing why a business exists, not what it exists to do.

“I couldn’t agree more with Simon,” he blogged. “At Virgin, we’ve always been driven by ‘why.’ Why do we do what we do? To be original, disruptive and have serious fun – to change business for good.”

As a spokesman, he is a master communicator and, on the Virgin.com blog, has also remarked often on the importance of clear lines of communication and clarity. To that end, he also intentionally creates small companies, because, he said, big companies aren’t nimble enough.

“I think big companies need to act like a small company and ideally break itself up into lots of little companies or get people who think like a small company,” he said. “That’s a challenge for a big company but with the right leaders it is possible to achieve.”

He’s already followed Bill Gates and Warren Buffett in pledging to give half his $4-billion fortune to charity, and in the interim remains a generous patron of many causes. More than that, though, he’s incorporated many avant garde concepts into Virgin’s business plan, such as investing $3-billion to promote the development and use of “green” aviation fuel.

“This could turn aviation from a dirty industry to one of the cleanest,” he blogged. “Within three years we aim to fly Virgin Atlantic planes with the new fuel on flights from Shanghai to London and Delhi to London.”

Sir Richard also recognizes innovation is a continuous quest, creating a “business innovation team” to work with all Virgin Group companies.

“Screw business as usual,” he blogs, which not so surprisingly is the name of one of his several books. “We’re here to make people’s lives better. Better means taking care of the people who work with us, the communities we operate in, and our planet. Life and work should be worthwhile, fun, and creative. It’s not just about working in a successful business but being able to make a difference while you’re at it.”

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